Frank Sinatra and The Mob

Sinatra's "hoodlum complex" only worked one way. While he was apparently enthralled with mobsters, ultimately the mob just used him the way they used anyone else—to make money and lots of it. But it would be unfair to characterize Sinatra as simply the mob's patsy. He was a complicated man whose life was defined by contradictions.

As a young man he had been investigated for sympathizing with radical left-wing Communists, but after being rejected by the Kennedys, he turned conservative, becoming a staunch supporter of Ronald Reagan.

Sinatra had always been a vocal supporter of civil rights and had made Sammy Davis Jr. an equal member of the Rat Pack at a time when black entertainers, no matter how famous, were not allowed to stay in the hotels where they performed. Yet Sinatra reveled in the company of wiseguys who as a group have never been known for their racial tolerance. (In a wiretapped conversation between Sam Giancana and one of his chief henchmen, Johnny Formosa, the two men vented their anger over Sinatra's failure to "deliver" President Kennedy. Formosa suggested that they "whack out" the entire Rat Pack to "show those a****** Hollywood fruitcakes." Referring to Sammy Davis, Jr., Formosa said, "I could take that nigger and put his other eye out.")

Sinatra was Hollywood royalty and often graciously acted the part, whether attending White House galas or receiving humanitarian awards for his charitable works. But he could also be crass and crude in public, cursing out underlings and making scenes when he was displeased. Kitty Kelly writes in her book His Way that on one occasion Sinatra spotted Godfather author Mario Puzo dining at Chasen's Restaurant in Los Angeles. Sinatra had always blamed Puzo's Sinatra-like character as one of the main reasons for his troubles regarding ties to organized crime. According to Sinatra's longtime friend and associate Jilly Rizzo, who was at the restaurant that night, Sinatra flew into a rage and loudly berated the author who finally got up and left in the middle of his meal. Sinatra shouted at the author as he walked away, "Choke. Go ahead and choke, you pimp."

Despite Sinatra's atrocious behavior and groupie passion for gangsters, he had enormous talents as a performer. He recorded many classic albums and single-handedly turned the American pop standard into an art form with his unique ability to "tell" a song. No other singer in any musical genre can match him in terms of longevity and consistent quality. Though he never gave his acting career the attention he gave to his music, some of his film performances, such as in From Here to Eternity, The Manchurian Candidate, Guys and Dolls, High Society, On the Town and The Man with the Golden Arm, will live on forever. Sinatra gave his last concert in November 1996. He died in 1998 at the age of 82.

If, as J. Edgar Hoover wrote, Frank Sinatra had a "hoodlum complex," perhaps he publicly suffered that syndrome for many men around the world who secretly harbor a desire to hobnob with enterprising outlaws, hoping to inspire a little fear and respect by association. Why else would Sinatra's rendition of his hit song "My Way" (lyrics by Paul Anka) become an anthem of manhood for so many American males? Like many of Sinatra's songs, it tells the story of his life—a grand, swinging, often reckless life that many men long for. As the song defiantly says, "The record shows/I took the blows/And did it my way."